


Double the Trouble

by lofticries



Category: The Umbrella Academy (TV)
Genre: Alternate Universe - Spies & Secret Agents, Blow Jobs, Dirty Talk, Dry Humping, Explicit Sexual Content, F/M, Fake-Out Make-Out, Fake/Pretend Relationship, James Bond References, Vaginal Fingering
Language: English
Status: Completed
Published: 2019-04-28
Updated: 2019-04-28
Packaged: 2020-02-08 19:06:55
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,660
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18629440
Author URL: https://archiveofourown.org/users/lofticries/pseuds/lofticries
Summary: Agent Five is a man with a mission. Vanya Hargreeves is the daughter of his mark. She's the key to his success in pulling this off.





	Double the Trouble

**Author's Note:**

> This was meant to be a drabble. Clearly, I got carried away. Originally based off Teddy's ask on tumblr [here.](https://igpitn.tumblr.com/post/184500059497/oh-man-i-just-saw-the-kissing-to-keep-our-cover) For simplicity's sake - this is completely AU. Five and Vanya don't know each other. Five is an agent working at The Commission, James Bond style. Vanya is the daughter of his mark. They're both meant to be in their mid to late twenties. Up to your imagination! This is just a very quick look into what kind of world this AU would entail. 
> 
> Also, porn because. It's _me._

 

 

> **Fake-out make-out:** when two people quickly kiss as a last resort in an emergency situation, often to cover up their previous actions so they don't get caught by others.
> 
>  

This is their fifth date, dinner at her father’s house, which pleases Five tremendously. This definitely speeds up his timeline since he wasn’t sure if Vanya would allow him over so soon. Hargreeves’ daughter is a quiet, guarded thing, a dark slip of a girl, really. He’d done his due diligence though and researched her thoroughly prior to the mission. Vanya Hargreeves, aspiring violinist, published writer, the only daughter and heir to billionaire Reginald Hargreeves. Also known as The Monocle, who’d been involved in the largest ring of human and drug trafficking in North America. Five’s employers have been waiting a long time to put him down, and he was the one who had the honor of doing it.

Vanya is the key. “Make friends with her, become her lover. I don’t care.” The Handler had instructed him. “Whatever it takes to get the information you need.” So Five put on his best civilized face and went to work. The girl plays third chair in her local orchestra and he’d gotten tickets to their latest concert.

He’d approached her after the show, praising her performance and posing as a fan of her published biography, a tale of how her life as an orphan changed when Hargreeves adopted her. She had been hesitant at his invitation for coffee but came out regardless. He figures she wasn't used to the attention and curiosity won her over. Five can work with that. He was a professional after all. The right pointed questions about her music made the tension bleed out of her shoulders the more she talked about the violin. She’d been notably silent about her father but that was fine with Five. Baby steps.

After Five finished his coffee, sipping as slowly as he could, he proposed meeting up again. Her cheeks had turned the sweetest shade of pink before nodding.

He grabbed her hand before she left, pressing a chaste kiss to her fingers. “It’s a date.” Her cheeks went even pinker.

So they go on a second date - a simple cafe lunch and the bookstore afterwards. Five is James to Vanya, a Cambridge graduate and an avid book reader. The Cambridge bit is fake, Five’s never been to college, every bit of his education unconventional with homeschooled math lessons intertwined with learning how to properly snap an enemy’s neck. But the books he enjoys, those are all real, and he and Vanya are able to have a genuine discussion over their favorites.

It goes so well, _she_ proposes the third date. An outdoor movie theater, playing _Casablanca._ The atmosphere is romantic; they have wine, he puts an arm around her shoulder and she leans into him. She kisses his cheek at the end of it.

Five’s in mission mode. Everything he does is for a reason. But Vanya Hargreeves is a delightful human being and after kissing her at the end of their fourth date, Five has to admit it - he actually likes her. The part of him that’s not focused on the mission, on bringing The Monocle down, genuinely likes her. Five has seduced women for his jobs before, it’s not a problem. His body is a weapon just as much as the glock strapped to his side.

But seducing Vanya? That’s not a job. He’s going to _enjoy_ every second of it.

The Monocle isn’t in tonight which Five decides is prodigious. After dinner, maybe he can convince Vanya to give him a tour of the house. Mansion, more like - it’s much too big for just Vanya and her parents. Five figures that one of these rooms contains valuable information regarding The Monocle’s underground work. Specifically locations holding either drugs or people. Ideally, one of these secret locations would be where Five would kill Reginald, leading the authorities to believe it was cartel-related violence, leaving his employers’ name out of it. They work in the shadows, after all.

“James?” Vanya’s sweet voice calling his cover-name interrupts his pondering. He snaps to attention, giving her his best disarming grin. Vanya blushes. His grin widens. She is so _cute._ “Do you want more wine?”

“Sure,” Five drawls, offering his glass to her. He’s going to kiss her today, he thinks to himself as she pours the wine, taking in the arch of her cheekbones, and her pursed, pink mouth. He’s going to kiss her today, kiss her _well_ and wrap her all around his finger. He pushes her to drink more as well, their dinner half-eaten and forgotten as their cheeks turn pink with the alcohol.

Five is considering what exactly to say to cajole her into touring the house when Vanya looks over at him demurely, batting her eyelashes. “Do you want to go up to my room?”

Five’s mouth goes dry. Would he _ever._ “I don’t want to impose,” he says stupidly instead of the charming line he means to reply with. Vanya just smiles at him and takes his hand. His heart pounds stupidly fast and she leads him up the stairs. This is most definitely an accelerated timeline. He wasn’t planning on sleeping with her until a little longer. Maybe next week. They’ve only been dating for two weeks after all. But if Vanya is showing initiative, Five will gladly play along.

He indulges himself for a moment, thinking about her soft skin under his hands and the scent of her hair. The sounds she’d make once he buried himself inside her, once he filled the space in between her legs. The way her body would move along with his thrusts… Shit, he’s getting hard just at the thought. He needs to get it together or he’ll end up embarrassing himself.

Vanya stops walking and he blinks at the large ornate door in front of them. “R. Hargreeves” is engraved at the top and Five is immediately confused. He looks over at Vanya, arching an eyebrow. “This… isn’t your room?”

Vanya regards him with an impassive expression. Her cheeks are still flushed but gone is the sweet look from before. Five blinks again. “No, but this is what you wanted to see. Right James?” She bites her lip. Five stares blatantly at her mouth. “If… that’s really your name?”

Wait a second. Five’s brain short circuits. What is she saying? She can’t mean… His body goes cold. No way. There is no way his cover is blown. No fucking way. He’d been careful, he’s _always_ careful. His backstory was foolproof - Ben had hacked Cambridge records just to be safe. She hadn’t been suspicious before. What went wrong?

He laughs a little, dropping a hand to her shoulder. Squeezing lightly. “What are you talking about, Vanya?” he asks lightheartedly. Deny, deny, deny. He doesn’t want to have to kill her. That was never part of the plan. Plus, he would not take _any_ pleasure in it.

Vanya’s eyes narrow. “I know what you are,” she tells him bluntly. “You’re here to kill my father.”

Five’s whole world freezes for one heart-stopping moment. It’s over. It’s fucking over. He’s going to have to kill her and call it a bust. Years of work, gone down the drain because of his incompetence. Then, Vanya restarts everything with her next words. “I’m not going to stop you. I want to help you.”

He gawks at her. Jaw dropped, and everything. He’s absolutely, one hundred percent, gobsmacked. Did he hear that correctly? Vanya… wants to help… _kill_ her father?

“I beg your pardon?” is all he manages to say. Vanya lets out a little huff, an adorable noise really, and rummages around in her cardigan pocket, producing a small key.

“This is dad’s main office. It’s one of the few rooms I don’t have access to,” she explains to him, completely bypassing his shock. “I stole dad’s key last week when he was hosting a dinner party. He didn’t notice! But, he’s always in here so this is our chance to sneak in.”

Five can’t stop staring at her. This… clever, clever girl. Not only did she figure him out, God knows how, she’s managed to successfully get a copy of the key so they can sneak into his office. Vanya is not only talented and sweet but full of cunning. It’s fantastic. It just makes her all the more attractive to him.

Five wants to kiss her. He wants to press her against the wall and drink from her mouth, feeling her body with his hands. He wants to bend her over the desk he’s sure exists in The Monocle’s office, and make her sing for him. He wants to _fuck_ her.

While he’s fantasizing, Vanya’s unlocking the door, looking back at him impatiently. “Quickly!” she hisses at him and Five’s mission mode immediately snaps into action. He drags her back before she can enter.

“Does your father keep cameras in that office?” he demands. Vanya looks bewildered.

“I’ve… never been in this room before. I don’t know.”

Five swears under his breath, rummaging in his pocket for one of Ben’s handy devices. He sure hopes The Monocle is a traditionalist and keeps a paper trail of important documents. It would be a bitch if he didn’t. He throws the tiny mechanical ball into the office, covering Vanya’s eyes and waiting for the tell-tale ‘pop’ of the lights shutting off, before pushing them both inside.

“What was that?” Vanya asks as Five begins rummaging through the office, sliding on a pair of gloves from inside his jacket. He picks up the device and stuffs it back into his pocket.

“It’s a little invention someone from my team made. Made to take out the electricity for a short period of time. So any cameras installed here are temporarily disabled.” He talks quickly and tersely, dropping his charming James act. No, he’s Five now and he’s got a job to do. “Don’t touch anything,” he tells her when he sees her reaching for the bookshelf. “Can’t leave evidence.”

Vanya’s eyes are bright. “You really are here to kill him,” she says with wonder. Her voice makes something hot burn in his gut.

No. Time to focus.

The Monocle has a large computer at his desk but Five doesn’t have the time to be able to properly hack into it, especially with the power down. He groans under his breath, opening the drawers as quickly as possible to try to find something of use. Vanya stands in front of him, watching him as he works.

“James,” she says urgently. “Look behind that painting.”

Five turns his head to the painting behind The Monocle’s desk. He carefully tilts it, whistling in approval when he sees a metal vault. He grunts a little as he lifts the painting off the wall, placing it down gently. The lock on the vault gleams mockingly at him. “Any ideas for the passcode in that pretty head of yours?” he calls back to Vanya.

She blushes. Five bites back a smirk. It’s good to know he can still make her blush. But then, her face goes blank. “Try zero-five-two-two.”

He does. It works. He looks at her, takes in the way she stares down at the ground, eyes vacant. “Is that your birthday or something?” Five asks quietly.

Vanya just shakes her head.

There’s no time for any more questions. Five looks back in the vault and sees it contains nothing but a manila folder. He opens it and swears loudly, making Vanya jump. “What? What?”

Five lifts the folder out of the vault reverently. “This is exactly what I need.”

Vanya blinks. “A folder?”

Five grins sharply. “A _list._ ” A list of contacts and locations, to be specific. Five couldn’t have asked for a better lead. It’s obviously in some kind of code but if he can figure out The Monocle’s network, he’ll have him right where he wants him.

He fumbles with the desk drawer, grabbing a piece of paper. “Come here,” he instructs. “Write down exactly what I say.” Five reads the list out loud and Vanya writes it down quickly in her neat handwriting. Once that’s done and he’s viewed her work with a critical eye, deeming it acceptable, he puts the folder back into the vault. Locking it once more and hanging the painting over it. Vanya sweeps her eyes over the office, pointing out a few places that Five messed up and he carefully puts everything back together.

They step out of the office together, Five shutting the doors and Vanya locking it once more. She lets out a deep breath, putting a hand over her chest. “That was _terrifying._ ” She laughs and now that Five snaps out of his mission mode, he can go back to enjoying her. Her smile is bright, exhilarated. She’s lovely. “I’ve never done anything like that in my life.”

“You’d be a good agent,” he tells her truthfully. She’d surprised him. People would naturally underestimate someone like Vanya which would make her perfect for this kind of role. It’s all too easy to imagine her working at his side. That thought brings him a strange sense of pleasure.

Her eyes shine when she turns her head to him. “You think?” She holds the paper to her chest. “James, I - “

There’s a sudden sound of the door downstairs opening and Vanya goes pale. “He’s not supposed to be home yet!” Vanya whispers in a tiny scared voice. Five quickly assesses the situation: they’re in front of Reginald’s office, Vanya looks guilty as hell, and Five is a stranger in his house. All things that would raise The Monocle’s suspicions.

“Which way to your room?” he hisses at her and she seizes his wrist, dragging him in the opposite direction. But there’s also the sound of footsteps coming up the stairs, right in front of their path, and Five’s breath quickens when he catches a glance of Reginald’s bald head below. He can’t be seen. Not like this. It’s too early.

“Vanya - “

He’s startled when she stops in her tracks, lifting her shirt to slide the paper up against her body. He gets one tantalizing glimpse of her taut stomach before he’s pushed against the wall and being insistently kissed.

For the second time today, Five’s brain short circuits. Vanya’s lips are soft and warm, her small body backing him up. He’s frozen against her, unresponsive for a few moments until Vanya tangles a hand in his hair and _tugs._

Five’s body goes on autopilot. He seizes Vanya’s waist and pulls her in closer until she’s pressed flush against him, feeling every delightful curve. The paper crinkles in between them. One hand goes up to tilt her head back so he can deepen the kiss, nudging her mouth open with his tongue. She lets out a very quiet moan and the sound stokes a fire deep inside Five. He can’t stop kissing her. He can’t stop touching her. He doesn’t _want_ to stop.

His dick twitches with interest in his jeans and he can’t help but roll his hips forward, letting her feel his desire for her. Vanya breaks the kiss for a moment, gasping for breath, her eyes wild. She looks at him, dazed and flushed. Five presses his forehead against hers, pressing quick kisses all over her cheeks before going for her mouth again. She tastes like the wine they had at dinner. She tastes _delicious._ He wants to sink to his knees and taste the rest of her.

Faintly he registers the sound of approaching footsteps. He quickly breaks the kiss to bury his face at her neck, keeping himself hidden, sucking at her sensitive skin, feeling her tremble in his hold.

The Monocle’s voice is clear and close. “Displays of youth are natural, child. But I’d like to see some restraint - keep this sort of thing in your room.”

Vanya digs her nails into Five’s shoulders. He bites down in response. “Yes, Dad. Sorry.” Her voice is breathy and beautiful and Five wants to hear more. But he stays still, the two of them entangled in each other and waiting for the sound of Reginald’s footsteps to fade. Vanya pulls away from him. “He’s gone into his room,” she whispers. There’s a bright red hickey on her neck, covered in his spit. Five can’t stop staring at it. She takes his hand again. “Come on.”

The walk to her room is quiet, Vanya pulling him inside quickly and locking the door. “Oh my god. I changed my mind. _That_ was terrifying.” She’s babbling, wringing her hands as she talks. “I don’t think he suspected anything. Honestly, Dad never cares about anything I do anyways so I’m pretty sure we’re in the clear.” She slides the paper from out under her shirt, giving him another teasing glimpse of her skin. “But just to be safe, maybe you should lie low - “

Five waits for her to place the paper on her desk. Then, he’s on her again in an instant, pressing her against her door and kissing her hungrily. Vanya gasps, stunned, against his mouth. “James - “ she moans. Five slides a knee in between her legs and she grinds down instinctively. One hand slides up her shirt to palm at her stomach, feeling it concave at her sharp inhale.

“That’s not my name,” Five breaks the kiss to murmur. “I’m _Five._ ”

She blinks up at him, the same dazed expression from before on her face. “Five…” she breathes quietly. A hot rush of desire floods him at the sound of his name in her voice. He grips her chin possessively, running his thumb over her cheek.

“Say it again,” he demands, rocking his knee upwards to grind up against her cunt. He’s never been so grateful for the invention of skirts until now. Vanya shudders, the back of her head hitting the door.

 _“Five,”_ she whines and Five can’t resist her any longer. He descends for another bruising kiss, the hand he’s got under her shirt moving up to paw at her breast, digging in past the thin cotton of her bra to tweak at her nipple. Vanya moans into the kiss, arching her body further into his hands, grinding shamelessly down on his knee. Her hands come to clutch at his back. She’s eager for him and that makes him crazy with want for her.

He bites down on her bottom lip, soothing it with his tongue when she whimpers. Too long he’s thought about her like this, desperate with desire, and he’s been thinking about fucking her all damn day. But he can’t stop himself long enough to push her to the bed, content to rock against her like this, his clothed erection bumping against her thigh. The friction is good even though it’s not nearly enough but there’s something incredibly delicious about having her like this. Minutes after she blew his mind with the knowledge that she knew he wasn’t what he said he was, after she helped him sneak into her father’s office, officially becoming his accomplice.

He’d already been fascinated by her and she’s proving out to be even better than he could’ve ever imagined.

Five breaks the kiss, burying his face into her hair to breathe her in, shamelessly groping her breasts and rubbing his cock all over her hip. Vanya’s breathing is hitched and ragged, a tiny gasp escaping her mouth every time he touches her just so. He can feel her panties getting wetter with every uninhibited grind against his knee.

“I don’t know how you saw through James,” he pants roughly into her ear. “Clever girl - keep your secrets, it’s alright with me.” He pinches her nipple again and she lets out a cry of his name. _Five._ It sounds so good on her lips. “Did you know what I planned on doing? I was going to become your _lover._ ” He emphasizes this with a shift of his hips, letting go of her face so he can lift her skirt, grinding himself right into her soaked center. Vanya lets out a high-pitched keen and he groans back at her, beginning to dry hump her in earnest. “I was going to sneak around the house while you were asleep and figure out your father’s secrets after all our dates.”

He turns his head so that he’s staring right at her, brown eyes blown nearly black with pleasure. She’s divine. Five wants to explore every inch of her, thoroughly, tirelessly. “I was going to fuck you.” She gasps. Five rocks his hips against hers insistently. “I wanted to fuck you. I _want_ to fuck you,” he growls, dropping her skirt to grab at her thigh, squeezing her soft skin. Vanya yelps, tossing her head back, exposing her throat to him. He scrapes his teeth over her exposed skin, leaving more marks.

“Do you want that Vanya?” he rumbles, tone dark and heavy with lust. His cock aches so bad, he feels ready to burst any second now, overcome in the heat of the moment and his desire for her.

“Yes,” she gasps. “I want it, yes, _please._ ” She sounds desperate for it and Five can’t resist anymore. He tugs his hand out of from under her shirt, holding her waist steady with one arm. His other hand slips into her panties, cupping her cunt. She’s so _wet_ , she lets out a sharp cry when his fingers touch her silky, soaked folds.

“Five, oh my god, Five,” she gasps brokenly as he slides his fingers into her, pumping and curling, making her shake. She leans forward, ready to bury her face into his chest, but he pushes her back. He wants to see her.

Vanya’s mouth is red, kiss-swollen, and parted in a sweet ‘o’ as she gasps and moans with every stroke of his fingers. Her hair is sticking to her sweat slicked skin, her neck covered in his bite marks. She looks ravished, and it’s all because of him.

Satisfaction spreads through his whole chest. He’s going to make her come for him, right in her childhood bedroom, his fingers deep in her cunt. “Later, I’m going to take my time with you,” he tells her, almost conversationally as he presses his thumb to her clit. She cries out loud, rocking her hips down with his movements. He’s going to toss her into her bed and rut into her until she cries. He’s going to take her back to that office and bend her over that desk. He’s going to fuck her in every damn room in this stupidly big house so that she’ll never be able to walk anywhere without thinking of him inside her.

Her nails dig into his shoulders and her entire body seizes while Five circles her clit. “I’m gonna come,” she gasps, eyes fluttering shut. Her wetness is dripping down his entire hand, cunt clenching exquisitely around his fingers. “I’m gonna - _ohmygod._ ”

She’s beautiful when she comes and Five commits every detail of it to memory, the sexy temor of her body, the way her mouth falls open, and the gorgeous cry she lets out, sharp and high. Her knees give out but Five catches her easily, pulling his hand out of her panties and licking up her slick from his fingers. Next time, he’s going to properly taste her.

With her finished, the throb of his cock in his pants is insistent and Five unbuttons his pants with a sigh, hand slipping into his boxers to stroke at his cock. He’s wondering just how to ask Vanya if she’d be up for a quickie when she surprises him _yet again_ by sinking to her knees, dragging his pants down with her.

“Oh,” he says dumbly once she grabs hold of his cock, looking up at him with those dark eyes. He shudders as she pumps him once, slowly. “Vanya. You don’t have to.”

She licks her lips. Five can’t tear his eyes away from her. “I want to.” She takes the head of his cock into her clever, sinful mouth and Five inhales sharply. He slides a hand into her hair, holding her lightly, hissing through his teeth as she takes him in further.

“Fuck, Vanya,” he growls when she starts sucking him in earnest. It’s messy, quick, and sloppy, her spit getting all over her chin and cheeks. But it’s perfect because everything about this encounter has been hurried and heated and Five can’t stop staring at the way his cock stretches her mouth, pushing at the inside of her cheek. He can’t help but touch her face and she closes her eyes, taking him in deeper.

He groans loudly when his cock hits the back of her throat. She moans right back, the vibrations around him making him tremble. He’s turning into putty at her touch, and he’s been so high strung after her the entire night, he can feel his release coming quick.

“Vanya, that’s enough,” Five tries to pull her off when that familiar tightening of his stomach comes around. Vanya pulls off long enough to speak.

“It’s okay. You can come in me,” she says, rendering him speechless. She goes back to work quickly after, bobbing her head on him, hand wrapped tightly around the base and Five’s a complete goner for her.

He’s been such a fool. Five never seduced her. Vanya seduced _him_ , plain and simple. He’s been gone for her since he met her and he didn’t stand a chance the minute she revealed she knew what he was.

He finishes in her mouth, cum shooting down her throat. His orgasm hits him like a flood, pleasure overtaking his body as he fucks into her willing mouth, prolonging the sensation. Vanya chokes a little at first but swallows and Five pets her hair as she does it.

“Good girl,” he gasps, shaking a little. He’s overwhelmed with sensation and with _her._ “Good fucking girl.”

Vanya wipes at the excess cum that dribbles out of her mouth and beams at him.

Afterwards, they curl up in her bed together, looking over the list they copied. “I don’t know what any of this means,” Vanya admits tiredly. Her head is resting right on his chest, while he holds up the paper for them to read.

Five yawns. “I’ll have to send it back to my team for analysis. But it’s a good start.”

Vanya’s quiet for a moment. She’s tracing circles on his arm. “Are you really going to kill him?” She asks it so quietly, Five’s not certain she actually said anything.

His jaw clenches. “Yeah.” He hesitates. Vanya had said she’d wanted to help him. Was that a fluke? If that’s the case, Five isn’t sure if he could handle it. Still, he needs to ask. “Do you… not want me to?”

She snaps her head back to face him. The look in her eyes is fierce and dangerous. Five’s heart pounds in his chest. “I want it,” she says determinedly. “And I’m going to help you. Every step of the way.”

The rational, logical part of Five, the one that’s been on countless missions, the one that knows involving civilians is not only a recipe for disaster but a violation of their guidelines, wants to let her down easy. Assure her that he’ll take care of the job and she can continue to live her life normally.

The other part of Five, the one that’s dangerously attracted to her, that’s been obsessing over how exactly she figured him out, doesn’t want that at all. He wants her by his side and he wants to see the look on her face when he finally pulls the trigger. Intimately. In a way he's never wanted anything before.

He presses a kiss to her temple. She relaxes in his hold. “Whatever you want, Vanya.”

And Five means it.

**Author's Note:**

> This was a LOT of fun to write and I hope you enjoy reading it! Comments keep me fed!


End file.
